Herbicide

ABSTRACT

New and valuable herbicide comprising a composition of several active ingredients.

United States Patent [1 1 [111 3,898,072

Fischer 1 Aug. 5, 1975 HERBICIDE [75] Inventor: Adolf Fischer,Mutterstadt, [56] References Cited Germany UNITED STATES PATENTS [73]Assignee; Badische Anilin- & Soda-Fabrik 3,689.50? 9/1972 Gates et al.71/92 Akti n h ft L d i h f 3,810,751 5/1974 Fischer et al. 7l/92(Rhine), Germany Primary E.\'aminerLewis Gotts [22] Flled' 1973Assistant ExaminerCatherine L. Mills [21] Appl. No.: 348,085 Attorney,Agent, or FirmJohnston, Keil, Thompson & Shurtleff [30] ForeignApplication Priority Data Apr. 13, 1972 Germany 2217698 [57] ABSTRACTNew and valuable herbicide comprising a composition [52] US. Cl. 71/88;71/92; 71/1 1 l of several active ingredients. 511 Im. Cl A0ln 9/22 i3Claims, No Drawings CH5- SO -OW on OC2H5 and b. a compound of theformula is however preferred to employ a ratio (by weight) ofazborcordoffromS l to l :5,preferably3 1 to l 3.

The agents according to the invention may be used as solutions,emulsions, suspensions, oil dispersions, granules or dusts. The form ofapplication depends entirely on the purpose for which the agents arebeing used; in any case it should ensure a fine distribution of theactive ingredient. V

For the preparation of solutions to be sprayed direct, mineral oilfractions of medium to high boiling point, such as kerosene or dieseloil, further coal-tar oils and oils of vegetable or mineral origin, andcyclic hydrocarbons such as tetrahydronaphthalene and alkylatednaphthalenes are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastesor wettable powders by adding water. To prepare emulsions theingredients assuch or dissolved in a solvent may be homogenized in wateragents, e.g., polyethylene oxide adducts. Concentrates where R denoteshydrogen, acetyl, propionyl or apt-dimethyl-B-acetoxypropionyl or d. acompound of the formula where X denotes hydrogen or lower alkyl of amaximum of 3 carbon atoms, has a good herbicidal action. The activeingredients may be mixed in any ratio; it

which are suitable for dilution with water may be prepared from activeingredient, wetting agent, adherent, emulsifying or dispersing agent andpossibly solvent. Oils of various types may be added to ready-to-usespray liquors.

-Dusts may be prepared by mixing or grinding the activeingredients witha solid carrier, e.g., kieselguhr, talc, clay or fertilizers.

Granules may be prepared by bonding the active ingredients to solidcarriers.

Directly sprayable dispersions may also be prepared with oils.

The new compounds maybe mixed with fertilizers, insecticides, fungicidesand other herbicides.

The new herbicides may be applied either preor post-emergence, and areparticularly suited for controlling dicotyledonous seed weeds andmonocotyledonous seed grasses in crops such as beet, spinach, potatoes,peas, beans and groundnuts.

EXAMPLE 1 In the greenhouse, loamy sandy soil was filled into pots andsown with beet (Beta vulgaris), lndian corn (Zea mays), commonlambsquarters (C henopodium album), wild mustard (Sinapis arvensis),smallflower galinsoga Galinsoga parviflora), slender foxtail(Alopercurus myosuroides), wild oat (Avena fatua), and barnyard grass(Echinochloa crus-galli). Subsequently the soil prepared in this mannerwas treated with the following amounts of the following activeingredients and compositions thereof, each active ingredient and eachcomposition being emulsified or dispersed in 500 liters of water perhectare:

I: 2-ethoxy-2,3-dihydro-3,3-dimethyl-5- benzofuranylmethane sulfonate,l, 1.5, 3 and 4 kg/hectare;

ll: 1-phenyl-4-amino-5-chloropyridazone-(6), 3 and 4 kg/hectare;

III: l-phenyl-4-( a-hydroxy-B,B,B-trichloroethylamino-S-bromopyridazone-(6), 1.5 and 3 kg/hectare;

l+ll: l 3 kg/hectare;

I+III: 1.5 1.5 kg/hectare.

The results given below show that the overall action of the compositionsis superior to that of their individual components.

Active ingredient l II I l-Hl l+lll kg/hu 1.5 3 4 3 4 l 5 3 1+3 l.5+l.5

Bela \ulgarLi- O 5 2O 30 l 0 5 O 5 Zea ways 0 0 35 0 15 5 l5 O 5 C/wrmmdium album lo 30 4O 6O 5O 65 60 100 90 I00 Sinapis arrz'nxix 7 l0 i5 455O 50 8O 55 100 95 95 Galinsuga parrifluru 1O 2O 4O 6O 4O 7O 50 100 809O Alupec-urus myaruruides 45 65 lOO I00 30 5O 40 90 100 I00 Arena falua40 60 100 lOO 2O 30 30 70 95 I00 Echinm'hlua ems-gull! 5O 70 100 lOO 3O3O 75 95 lOO 0 no damage 100 complete destruction EXAMPLE 2 l 5 foxtail(Alopecurus myosuroides), and annual bluegrass Poa annua were treated ata owth hei ht of 3 to 13 In the greenhouse, seeds of beet (Betavulgarzs), h th f n gr f h f l cm Wlt e o owing amounts 0 t e o owingactive common ambsquaners (Chenopodmm album) ingredients andcompositions thereof each active inmustard (Sinapis arvenis), slenderfoxtail' (Alopecurus mvosuroides) and wild oat (Avena fatua) were sownin gredlen-t and each composmon bemg emulsified or dis- 20 persed in 500liters of water per hectare: loamy sandy S01] and subsequently treatedwith the fol- I: 2 ethoXy 2 3 dihydro 3 3 dimethyl 5 lowing amounts ofthe following active ingredients and benzofuranylmethane sulfonate O 5 11 5 2 and 3 Q 9 1 compositions thereof, each active ingredient and each(g/hectare. composition being emulsified or dispersed in 500 liters I]:3 b l i h n l-N-(3 '-methylof wate Per hectare phenyl)-carbamate, l and2 kg per hectare;

l: 2-ethoxy-2,3-dihydro-3,3-dimethyl-5- benzofuranylmethane sulfonate,1.5, 2 and 3 kg/hectare;

ll: 1-( a, a-dimethyl-B-acetoxypropionyl)-3-cyclohexyl- 5,6-trimethyleneuracil, 1.5 and 3 kg/heetare;

lll: 3-cyclohexyl-5,o-trimethylene uracil, 1.5 and 3 kg/hectare;

l+Il: l.5 l.5 kg/hectare;

l+lllz 1.5 l.5 kg/hectare.

The following results show that the compositions have a betterherbicidal action than their individual components, combined with goodcrop plant compatibility.

Ill: l-phenyl-4-amino-5-chloropyridazone-(6), 2 and 3 kg per hectare;

IV: 1 -phenyl-4-( a-hydroxy-B,B,B-trichloroethylamino-5-bromopyridazone-(6), 1.5 and 2 kg/hectare;

V: l-( a,a-dimethyl-B-acetoxypropionyl )-3-cyclohexyl 1+1: 1 2kg/hectare;

l-HV: 0.5 1.5 kg/hectare; I+Vz l.5 0.5 kg/hectare; I-l-Vl: 1 lkg/hectare.

lll H-ll Active ingredient I ll l-Hll kg/ha l 5 2 3 l 5 L5 3 l.5+l.5 l5+1.5

Bela vulgaris 5 IO 20 0 3O 0 4O 5 5 Clzelm mdium album 20 3O 4O 90 35 9O95 85 Sinapis an'ensis 15 2O 35 95 4O lOO 95 80 Alupez'urus m\'0suruides 85 100 30 25 75 100 100 Arena falua 6O I00 25 55 2O 70 lOO95 0 no damage 100 complete destruction EXAMPLE 3 The plants beet (Betavulgaris), common lambsquar- 55 ters (Chenopodium album), chamomile(Matricaria clzamomilla), wild mustard (Sinapis arvensis), slender After2 to 3 weeks it was ascertained that the compositions had a betterherbicidal action than their individual components, combined with goodcrop plant compatibility.

"lhe results are given below:

lll lV Active ingredient I ll kg/hu 0.5 l l 5 2 3 l 2 2 3 L5 2 Betai-ulgaris 0 0 5 20 30 O 20 0 0 O O Chenopodlum album 10 20 35 50 7O 80100 65 90 6O Marricuria chamomilla 2O 30 5O 70 35 80 60 90 65 90 SinapixGIVL'HSl-Y l() 20 40 60 90 75 50 85 6O 80 Alopecurus nrvosuroizlas 3O 5O60 100' l()() l0 15 4O 80 4O 50 Poa amma i 25 45 55 904 100: l 10 20 3575 45 6O -Continued Active ingredient V VI 1+11 1+111 1+1V l+V 1+V1kg/ha 0.5 2 l 2 1+1 1+2 0.5+1.5 0.5 1+1 Bela vulgarix 20 25 0 O 0 5 5Chcnupudium album 30 100 50 100 100 100 100 95 95 Marric'aria (Immomillu35 95 40 90 100 100 95 100 100 Sinapix arrensix 40 100 65 100 100 100100 g 100 100 Alopecurus m \'0sur0ides 25 95 45 9O 90 100 95 100 100 Funannua 30 100 45 90 85 95 90 100 100 0 no damage 100 complete destructionEXAMPLE 4 I: l-pheny1-4-amino-5-ch1oropyridazone-(6), 0.2, 0.25,

0.5, 0.75, l and 1.2 kg/hectare;

1-ethoxy-2,3-dihydro-3 ,3-dimethy1-5- benzofuranylmethane sulfonate,0.2, 0.25, 0.5, 0.75, l and 1.2 kg/hectare; 1+1]:

0.25 0.75 kg/hectare; 0.5 0.5 kg/hectare; 0.75

0.25 kg/hectare.

After 3 to 4 weeks it was ascertained that the compositions had a betterherbicidal action than their individual components compared with thesame good crop plant compatibility.

The results are given below:

Active ingredient 5,6-trimethy1ene uracil, 0.5, 1, 1.5 and 2 kg/hectare;kg/ha 0.5 0.75 l 1.2 I II. 3-methoxycarbony1ammopheny1-N-(3 -methyl- 3OBela w 11g m 0 O 0 0 0 O phenyl)-carbamate, 0.5, 1, 1.5 and 2kg/hectare; Zea mays 0 0 0 0 0 0 l+n cheno mdium album 8 1O 25 42 Galiumapariue 8 10 15 30 40 42 1 1 kg/ hectare; Galiusoga 0.5 +1.5 kg/hectare;m fl rq 8 10 2o 25 30 32 l 5 0 5 k t 5 Mamc'arlu g CC 2116- cliamumillu13 15 30 4O 5O 52 After 6 to 10 days it was ascertained that the compo-P lvgvnum 8 pzrslcaria IO 20 35 3O 32 s tions had a stronger herbicidalaction than their lndi Sinai, Helms 8 lo 20 30 47 vidual components:Alopecurus Active ingredient 1 11 [+11 0.5+ 1.5+ kg/ha 0.5 1 1.5 2 0.5 11.5 2 1+1 1.5 0.5

Bela i'ulgaris 0 O 5 20 O 0 1O 25 O 10 5 Sinapis unensis 25 45 60 95 254O 70 95 100 100 100 Chenopodium album 20 4O 85 30 5O 80 100 100 100 100Mam'caria chamumilla 3O 50 75 95 20 30 85 100 100 100 Galium aparine 2540 60 85 15 3O 50 95 95 100 Alapecurus myvsuroides 25 45 95 5 1 0 1 5 2075 100 Poa annua 20 40 65 9O 5 1O 15 2O 8O 7O Echinochlna crus-galli 2040 60 85 10 1 5 20 3O 85 70 95 0 no damage complete destructionnlyosuruides 2 3 6 9 1 1 1 3 EXAMPLE 5 5 Arena farua 2 3 5 8 10 12 Anagricultural plot was sown with seeds of the plants 3 5 8 lo I 3 l 5given in the table below. The soil was then immediately no damagetreated with the following amounts of the following acn tive ingredientsand compositions thereof:

Active ingredient 11 kg/ha 0.2 0.25 0.5 0.75 1 1.2

Beta rulgaris 0 0 0 0 0 0 Zea may 0 0 O O O 0 Chenupodium album 2 3 5 810 13 Galium aparine 4 6 10 14 20 22 Gulinsoga parwfluru 1 2 5 8 10 1 1Malricaria chammnillu 4 5 9 16 22 24 Polygouum persiz'ariu 3 S 8 14 1820 Sinapix arreuxis 2 3 5 8 10 l 1 C ontinucd Active ingredient II k /hn0.2 0.25 0.5 0.75 1 1.2

Alopecurus m \'aruruide.v 8 10 I5 30 45 47 Arena falua 8 I0 4O 41Ecliinwlzloa crus- 'alli l2 15 30 40 50 52 Active ingredient I+II I+III+II I+II I-l-II 025+ 0.5+ 075+ 0.2+] I+0.2 kg/ha 0.75 0.5 0.2.5 Betavii/gun's- O 0 0 O O Zea mays 0 0 O 0 0 Chenupodium album 25 25 48Galium aparine 30 3O 33 Ga1in.s'ugu parviflura 25 30 35-40 22 35Malricaria clmmomillu 35 45 50 40 58 Pub-gum): persican'a 28 35 45 32 39Sinapis arvensis 25 30 22 53 Alupecurus mymumides 40 25 25 53 25 Arenafarm: 38 3O 22 46 23 EC/IIIIULIIIULI crus-galli 5O 42 30 60 30 0 nodamage 100 complete destruction EXAMPLE 6 EXAMPLE 7 1 5 kg/hectare; 5 1kg/hectare;

I+III: 1 5 kg/hectare (not according to the invention) In thegreenhousevarious plants were treated at a growth height of from 3 to 11 cm withthe following amounts of the following individual active ingredientsand'compositions thereof as oil dispersions:

I: 2-ethoxy-2,3-dihydro-3,3-dimethyI-5-benzofuranylmethanesulfonate,0.25, 0.5, 0.75 and 1.0 kg/ha;

l-phenyl-4-amino-S-chloropyridazone-( 6) 0.25

0.5, 0.75 and 1.0 kg/ha;

III: 3-cycIohexyl-5,6-trimethylene uracil, 0.25, 0.5,

0.75 and 1.0 kg/ha; I 1+ 11: 0.25 0.25, 0.25 0.75 and 0.75 0.25 kg/ha;I+ III: 0.25 0.25, 0.25 0.75 and 0.75 0.25 kg/ha.

After 2 to 3 weeks it was ascertained that the compositions had a betterherbicidal action than their individual components, combined with thesame good crop plant compatibility.

The results of this experiment are given below:

After 3 to 4 weeks it was ascertained that the compo- Active ingredient1 sition of I II had a better herbicidal action than its ink dividualcomponents and the composition of I III 40 Crop plants; (non-inventive),combined with the same good crop Bela 8 0 0 0 0 l t Unwanted plants: PComp21 1 11 Y; Avenafalua 18 30 40 5s The results are given below:Bromus rec-10mm 30 35 43 60 Active ingredient II I III kg/ha 6 5 l 6 S l6 5 1 Bela \ulgarix 40 20 O 5 O 0 I00 20 C/unopudium album 55 45 10 100100 40 I00 I00 20 Gulium aparine 80 80 20 I00 I00 40 I00 90 I5 Galinsoguparriflura 60 50 I0 I00 I00 30 80 I5 Marni-aria (/IUIHUHII/[ll 80 22 100I00 50 100 I00 20 Puhyonum penvicariu 80 70 18 100 I00 30 100 I00 20Simlpis w'vensis 60 50 10 100 I00 45 90 I5 Alupet'urux myuxuroidcs I0045 60 50 1 1 70 60 10 Active ingredient II I III kg/ha 6 5 I 6 5 I 6 5 1Aw'mlfulua I00 I00 40 55 45 I0 80 7O 15 Ec'lzinuclllua crns-gulli 100I00 50 70 60 13 7O 60 10 Active ingredient I+II I+II I+III kg/hu 1+5 5+11+5 Bela \ulgul'Ls' 20 0 80 Chenopmlium album 90 100 I00 Gulium uparineI00 I00 I00 Galinsugu purriflom 90 I00 I00 Murricuriu clmnmmillu I00 I00I00 l0l \gunum pertricuriu I00 I00 100 Sinupis w'rensix I00 I00 I00Aluperurux myoxuruides 100 I00 80 Arena farm! I00 I00 90 Echinoz'hlmlc'rm-gtlI/i I00 I00 80 0 no damage 100 complete destruction -ContinuedActive ingredient l+lll kg/ha 0.Z+O.75 O.25+O.25 O.75+O.25

Active ingredient l kg/ha 0.25 0.5 1.0 crop plums:

Malrican'a (/ltllllUNlilltl l5 23 34 8 0 0 0 Scturiu faln'ri'i 33 49 60Unwanted plants:

Sinapis arvensix 8 15 24 j 75 60 82 Q no damage Bronius reclurum 80 8085 100 complete destruction Marril'uria clianiumilla 76 62 72 Semriafaherii 8O 83 95 Sinapis anensis 80 65 80 Active ingredient ll 0 nodamage kg/ha 0.25 0.5 i0 100 complete destruction Crop plants:

Bela i'ulgariii" O 0 O Unwanted plants:

Arena fama 7 ll 15 EXAMPLE 8 Bron us ten-mm 5 l0 25 M"' 35 45 In thegreenhouse various plants were treated at a .Setaria jiberii 8 l lSinai, Wrens. 23 34 40 growth height of from 2 to 11 cm with thefollowing 0 no damage amounts of the following individual activeingredients mpme destructon and compositions thereof as pastes:

l: 2-ethoxy-2,3-dihydro-3,3-dimethyl-5- Active ingredient mbenzofuranylmethanesulfonate, 0.15, 0.25, 0.5, 0.75,

kg/ha 0.25 0.5 1.0 1.0, 1.25, 1.5, 1.65, 2.0, 3.0 and 4.0 kg/ha;

C I. t ll: l-phenyl-4-amino-5-chloropyridazone-(6), 0.15,

Qj f Z'LZ- O O 0 0.25, 0.5, 0.75, 1.0, 1.25, 1.5, 1.65, 2.0, 3.0 and 4.0

Unwanted plants: kg/ha; V

Arena fzuua l0 15 Bmmus Imam" I5 25 III. 3-cyclohexyl-5,6-trimethyleneuracil, 0. l5, 0.25,

Mutrit'aria c'l tmiuniilla 15 24 0.5, 0.75, 1.0, 1.25, 1.5, 1.65, 2.0,3.0 and 4.0 kg/ha;

Siriu m' urvensm 25 35 7O O no damage and 4 kg/ha,

100 complete destruction l-l-lll 0.25-l-O.75, 0.25-l-0.25, 0.75-Hl25,O.5+0.5, 0.25-i-L25, 1.25-l-O.25, 0.75+O.75, 1.5+0.15, 0.l'5+l.5,3.0+l.O, 1.0-HI) and l.O+3.0 kg/ha;

k iil i g i 0 7 l-Hll: O.25+().75, 0.25-l-0.25, O.75+O.25, 0.5+O.5,

Crop plants: 0.15-i-l.5, 3.0+l.0, 1.0-FLO and l.0+3.0 kg/ha;

Bela \ulgw'is 0 0 0 I-l-IV: 1.0+3.0 kg/ha.

Unwanted plants:

fama 70 75 After 2 to 3 weeks it was ascertained that composi- Bmn ux emrum 85 60 tions [+11 and [+1]] had a better herbicidal action than 8562 77 the individual ingredients I, l1 and combined with s mi-i ifizbcrii 72 70 the same good crop plant compatibility, and better gfgzgj 60 80 crop plant compatibility than active ingredients IV and 100complete the composition 1 IV.

desmmlo The results are given below:

Active ingredient l kg/ha O.l5 0.25 0.5 0.75 l.O 1.25 1.5 l.65 2.0 3.04.0

Crop plants:

Bela i'ulgaris O O O 5 lo 20 3O 35 Unwanted plants:

Arena falua 25 35 5O 6O 6O 65 7O 80 100 Bmmus IEL'IOIUIH 30 40 55 58 6364 75 80 I00 Mam'c'aria cliziniomilla 2O 23 3O 35 5O 6O 70 I00 Semriafaherii 35 45 55 6O 7O 7O 90 I00 Sinapi'r arvem'ix l0 15 20 28 40 50 6O9O lOO 0 no damage lOO complete destruction Active ingredient ll kg/ha0.15 0.25 0.5 0.75 1.0 1.25 1.5 L65 2.0 3.0 4.()

Crop plants:

13cm vulgar-is O O O O O (l O 0 O 0 l0 Unwanted plants:

Aiemifumu l 3 8 l0 l2 l5 l8 25 3O 45 Bro/mm" Iecwrum (l 5 15 O 22 28 293O 35 70 Mulri'curi'u (/lUInUIlii/[tl 7 10 3O 35 4O 45 50 52 6O 90 100Seluriu faberi'i l 3 l0 0 25 3O 30 33 4O 5O Sinnpi's arveniis 15 2O 3033 35 40 44 45 5O 85 100 O no damage 100 complete destruction 13 140.25, 0.5, 0.75, 1.0, 1.25, 1.5, 1.65, 2.0, 3.0 and 4.0 the individualactive ingredients I, 11 and 111 combined kg/ha; with the same good cropplant compatibility, and better 111: 3-cyc1ohexyl-5,-trimethylene uracil0.15, 0.25, crop plant compatibility than active ingredient IV and 0.5,0.75, 1.0, 1.25, 1.5, 1.65, 2.0, 3.0 and 4.0 kg/ha; the compositionI-HV. 1V: N-(4-bromophenyl)-N-methoxy-N'-methylurea 3 5 The results aregiven below:

Active ingredient l kg/ha 0.15 0.25 0.5 0.75 1.0 1.25 1.5 1.65 2.0 3.04.0

Crop plants: Beta rulgarix 0 0 0 O 2 6 1O 20 30 Unwanted plants: Arenafaluu 2 5 16 21 4O 50 60 65 80 100 100 Bromus lecmrum 3 5 14 18 25 30 3537 50 70 100 Malricaria clzammnillu 6 1O 20 3O 40 45 50 53 70 90 I00Selaria faberii 11 20 30 40 5O 60 75 8O 90 100 100 Sinapis an'ensis 0 05 5 10 l3 18 19 2O 35 50 O no damage 100 complete destruction Activeingredient l1 kg/ha 0.15 0.25 0.5 0.75 1.0 1.25 1.5 1.65 2.0 3.0 v 4.0

Crop plants: Bem rulguris 0 0 0 0 0 0 0 0 0 0 l5 Unwanted plants: 1Arena fa/ua 0 O 2 5 6 8 15 18 30 Brumus lecmrum 0 O 5 7 10 13 15 17 2230 35 Matricaria c'lm/nomilla 7 8 10 18 5 30 45 47 60 90 100 Semriafuberii 4 6 10 14 2O 35 37 40 60 65 Sinapis arvensix 10 15 20 "5 3O 3550 55 60 70 8O 0 no damage 100 complete destruction Active ingredientlll kg/ha 0.15 0.25 0.5 0.75 1.0 I 1.25 1.5 1.65 2.0 3.0 4.0

Crop plants: Bela vulgaris 0 O 0 0 0 0 0 0 10 40 50 Unwanted plants:Arena falun 3 5 1O 15 18 2O 23 25 50 70 95 Bronms rectarum 12 18 25 3540 50 60 65 75 100 100 Maln'caria chamomillu 1O 20 40 56 7O 80 85 90 100100 100 Setaria faherii l0 15 25 34 4O 46- 55 6O 7O 75 83 Sinapisan'enxis 7 10 2O 38 43 50 70 100 100 0 no damage 100 completedestruction and 4 kg/ha; Active ingredient I 1V 1+; 0.25+0.75,0.22+0.25, 0.75+0.25, 0.5+0.5, kg/ha 0.25+l.25, 1.25+0.25, 0.75+O.75,1.5-+0.15, c plants; 0.l5+1.5, 3.0+1.0, and l.O+3.0 kg/ha; 3 85: 100 100nwante p ants: H-lll. 0.25+O.75, O.25+O.25, 0.75+0.25, 0.5+0.5, Avenafamu 100 I00 0.25-1-1.25, 1.25-1-0.25, 0.75-1-0.75, 1.5-1'0. 15, 45Bromus lecturum 100 100 Manic-aria chamumilla 100 100 0.l5+1.5, 3.0+l.O,l.O+1.0 and l.O+3.0 kg/ha, Semriafabem. 80 loo H-IVZ 1.0+3.0 kg/ha.Sinupis arvensis 100 100 After 3 to 4 weeks it was ascertained thatcomposi- 0 damage tions 1+1! and I+l11 had a better herbicidal actionthan Active ingredient H-ll kg/ha 0.25+0.75 0.25+O.25 0.75+0.25 0.5+O.50.25+1.25 1.25+0.25

Crop plants:

Beta \ulgaris 0 0 0 0 0 2 Unwanted plants:

Arena fatua 45 30 55 45 90 95 Bromus tectorum 26 52 50 55 70 Mnlricariachamomilla 80 5O 70 82 85 80 Selarin faberii 85 70 70 9O 95 Sinapisan'ensis 55 40 50 53 80 75 O no damage 100 complete destruction Activeingredients H-ll kg/ha 0.75+0.75 1.5+0.15 0.15+l.5 3.0+].0 l.0+l.0l.0+3.0

Crop plants:

Bela vulgaris 0 5 0 20 O 0 Unwanted plants: A

Avena falua 85' 80 100 95 100 Bromus ILl'IOIlHH 72 55 50 100 75 100Malricaria chamumilln 88 75 100 95 100 Selariu faberii 97 92 100 100 100Sinapis arvensis 82 7O 80 95 85 0 no damage 100 complete destructionActive ingredients l-Hll kg/ha 0.25+O.75 0.25+O.25 0.75-+0.25 0.5-+0.50.25+1.25 1.25-l-0.25

Crop plants: Beta i'ulgaris O O 0 VO 2 Unwanted plants: Avena fatua O 3O55 56 70 85 Bramus rec-mm 7O 52 68 70 8O 85 Mulric'ariu clzumomilla 856O 8O 83 100 [GO Semria fuberii 83 65 85 86 90 95 Sinapis an'ensis 6O 355O 55 75 80 O no damage 100 complete destruction Active ingredientsl-Hll I-HV kg/ha 0.75+0.75 l.5+0.l5 O.15+l.5 3.0+! .0 1.0+l.0 1.0+3.0l.0+3.0

Crop plants: Bela vulguris O 5 O 0 40 100 Unwanted plants: Arena faluu80 9O 80 I00 95 100 100 Brumus tecmrmn 8O 9O 85 I00 95 I00 100Malricaria chamomilla 100 100 100 100 I00 I00 100 Scturiu faberii 92 95100 100 100 100 lOO Sinapis ari'ensis 76 75 7O 95 70 100 100 O no damage100 complete destruction EXAMPLE l0 ual components, combined with thesame good crop An agricultural plotwas sown with the seeds of vari-Plant p tl lll yous plants. The soil prepared in this manner was thenThe results are given below:

Active ingredients I 11 Ill kg/ha 0.25 0.5 0.75 1.0 0.25 0.5 0.75 1.00.25 0.5 0.75 1.0

Crop plants: Beta rulgaris 0 O O O O O O 0 0 O O O Unwanted plants:Arena falua 5 16 21 4O 0 2 5 6 5 10 l5 l8 Bromus lecwrum 5 l4 18 25 O 57 1O 18 25 Malricaria chamomilla 10 2O 3O 40 8 l0 I8 25 2O 40 56 70Semria faberii 20 30 40 50 6 l0 14 20 I5 25 34 40 Sinapis anensis O 5 5l0 15 2O 25 3O 1O 20 3O 35 O no damage 100 completevdestruction Activeingredient l+ll l-Hll kg/ha o.25+0.75 0.25-+0.25 0.75-+0.25 0.25-H1750.25-+0.25 0.75-+0.25

Crop plants: Beta rulgaris O O 0 O O 0 Unwanted plants: Avenafanm 3O 5530 Brahms rec-10mm 50 26 52 70 52 68 Mam'cana clzumomilla 8O 50 7O 85 8OSetaria faberii 85 7L 7O 83 85 Sinupis an-ensis 55 40 50 6O 35 50 O nodamage complete destruction immediately treated with the followingamounts of the EXAMPLE 11 following active ingredients and compositionsthereof 55 In the greenhouse Various plants were treated at a m the formof granules: growth height of 3 to l 1 cm with the following amounts 1:z'ethoxy'23'dihydro33'dimemthyl-5 of the following active ingredientsand compositions benzofuranylmethane sulfonate, 0.25, 0.5, 0.75 and h fas dispersions; 10 kg/ha; 60 l: 3-cyclohexyl-5,o-trimethylene uracil,0.1, 1.0 and 1.2 II: 1 -phenyl-4-amino-5-chloropyridazone-( 6), 0.25 k/h and g/ ll: 3-methoxycarbonylaminophenyl-N-(3'-methyl- Ill:3-cyclohexyl-5,6-trimethylene uracil, 0.25, 0.5, phenyU-Ca and g/ 0.75and 1.0 kg/ha; lll: 1-phenyl-4-amino-5-chloropyridazone-(6), 0.1, 1.01+: 0.25-+0.25, 0.25-H and 0.75-+0.25 kg/ha 65 and 1.2 kg/ I+Ill:0.25-+0.25, 0.25-10.75 and 0.75-+0.25 kg/ha. I+ll+lll1 0.1+O. 1+].0.O.l+l.O+O.l and 1.0+O.1+0.l

After 2 to 3 weeks it was ascertained that the 'compog/ sitions had abetter herbicidal action than their individ- After 2 t0 3 ks it a as a tthe P kg/ha. After 2 to 3 weeks it was ascertained that the compositionshad a better herbicidal action than their individ- Active ingredient 1kg/ha 0.1

Crop plants: Beta vulgaris Unwanted plants: Avenu fatua Brumus lectorumMaln'caria chunmmillu Setaria faberii Sinapis arvensis O no damage 100complete destruction Active ingredient: kg/ha Crop plants: Beta vulgarisUnwanted plants: Arena fatua Brumus lecwrum Malricariu chamomillaSelaria faberii Sinapis an'enxis O no damage 100 complete destructionEXAMPLE r2 7 In the greenhouse, various plants were treated at a ualcomponents, combined with the same good crop plant compatibility.

The results are given below:

Active ingredient 1 11 111 kg/ha 0.1 1.0 1.2 0.1 1.0 1.2 0.1 1.0 1.2

Crop plants: Beta vulgaris 0 0 0 0 0 0 0 0 0 Unwanted plants: Arenafatua 8 56 2 20 23 1 l0 1 l Bromus lectorum 12 57 2 l5 l8 0 20 21Malricaria chamomilla 3 3O 33 5 35 39 5 4O 44 Selaria faberii 8 S5 58 32O 23 1 2O 24 Sinupis an'ensis 1 2O 26 8 81 I3 35 39 0 no damage 100complete destruction Active ingredient l+ll+lll l+ll+lll l+ll+lll kg/ha0.1+O.1+1.0 0. 1+1 .O+0.l 1.0+0. l+0. 1

Crop plants: Beta vulgaris O 0 0 Unwanted plants: Arena falua 78 8O 9OBromus lectorum 87 90 Malricaria clzamomilla 90 85 65 Semria faberii 8O83 95 Sinapis arvensis 95 75 0 no damage 100 complete destruction growthheight of 3 to l 1 cm with the following amounts EXAMPLE 13 In thegreenhouse, various plants were treated at a growth height of 3 to 12 cmwith the following amounts of the following active ingredients andcompositions thereof as emulsions: I I: 3-cyclohexyl-5,-trimethyleneuracil, 0.1, 0.25, 0.5,

0.75, 1.0 and 1.1 kg/ha;

3-methoxycafbonylaminophenyl-N-( 3 '-rnethylphenyl)-carbatfi flte, 0.1,0.25, 0.5, 0.75, 1.0 and 1.1 kg/ha;

[+1]: 0.25-+0.25, O.25+O.75, O.75+O.25, 0.5-H15, X

0.1+1.0 and 1mm kg/ha. Y

After 2 to 3 weeks it was ascertained that the compo sitions had abetter herbicidal action than their individ- N O ual components,combined with the same good crop 5 plant compatibility.

The results are given below:

Active ingredients I ll kg/ha O.l 0.25 0.5 75 L0 1 l 0 l 0.25 0.5 0 75 lO l 1 Crop plants: Bela vulgaris O O O 0 O O O O 0 O O 0 Unwantedplants: Arena falua 2 1O 20 3O 32 2 5 l0 22 Brvmus lecmrum 3 10 20 25 372 3 8 l2 l5 l6 Mulricaria clzanzomilla 4 l0 2O 30 40 42 5 l0 I8 25 35 38Semria faberii 3 l5 20 25 I 35 37 3 6 10 15 20 21 Sinapis an-ensis l2 203O 35 65 68 8 l6 35 5O 75 80 0 no damage lOO complete destruction Activeingredients l-Hl kg/ha 0.25-+0.25 0.25+0.75 0.75+0.25 0.5+O.5 0.l+l.0l.0+0.l

Crop plants: Beta vulgar-is O O O O O O Unwanted plants: Arena falua 3O6O 50 5O bramus lecmrum 4O 6O 63 61 55 65 Malricaria chanmmillu 45 65 7O62 78 Semria fuherii 46 68 7O 65 67 7O Sinupis anemia 60 95 93 100 mo 0no damage lOO complete destruction EXAMPLE 14 30 where Y denotes chloroor bromo, X denotes amino, in

In the greenhouse various plants were treated at a a weight to bin therange of 10:1 to 1:10

growth height of 4 to 12 cm with the following amounts of the followingactive ingredients and compositions thereof as concentrated sprayliquors:

I- 2-ethoxy-2,3-dihydro-3,3-dimethyl-5- 2. A herbicide composition asclaimed in claim 1, wherein said weight ratio is 3:1 to 1:3.

35 3: A herbicide composition as claimed in claim 1,

wherein compound b is l-phenyl-4-amino-5- chloropyridazone-( 6 4. Aherbicide composition as claimed in claim 3,

40 wherein said weight ratio is 3:1 to 1:3.

5. A process for suppressing growth of undesired or weed plants in cropplants which comprises applying to the host soil for said plants aherbicidally effective 45 amount of a mixture of plant compatibility.

a a compound of the formula The results are given below:

Active ingredients I ll lll kg/ha 0.] 0.5 0.9 1.0 0.] I 0.5 0.9 L0 0.H09 1 0.5+O.5

Crop plants: Bela rulgaris O O 0 O O O O O 0 O O Unwanted plants: Arenafulua 8 25 48 5O 2 l0 l9 20 80 70 Brown: lecmrum l2 3O 50 55 2 8 l4 I585 95 80 Marricaria clmmomillu 3 20 28 30 5 i8 33 35 7O 60 68 Semriuberii 8 35 52 5S 3 l0 19 2O 88 96 86 Sinapis ("'VLHSiS 1 l0 l8 0 8 35 7275 100 80 80 0 no damage 100 complete destruction 1 claim: CH

1. A herbicide composition comprising a herbicidally CH S 0 O CHeffective amount of a mixture of 60 5 5 a a compound of the formula O 25 5 6H SO -0 CH O OC H and and b a compound of the formula b a ompound fth f rmu a CH5 cu -so -occjj ca o oc a and b a compound of the formulawhere Y denotes chloro or bromo, X denotes NH--- CHOHCCL in a weightratio of a to b in the range of 1:1 to 1:3.

10. A process for suppressing growth of undesired or weed plants in cropplants which comprises applying to the plants themselves a herbicidallyeffective amount of a mixture of a a compound of the formula and b acompound of the formula X (Y n o where Y denotes chloro or bromo, Xdenotes amino, in a weight ratio ofa to b in the range of 10:1 to 1:10.11. A process as claimed in claim 10, wherein said weight ratio is 3:1to 1:3.

12. A process as claimed in claim 10, wherein compound b isl-phenyl-4-amino-5-chloropyridazone-(6). 13. A process as claimed inclaim 12, wherein said weight ratio is 3:1 to 1:3.

1. A HERBICIDE COMPOSITION COMPRISING A HEBICADALLY EFFECTIVE AMOUNT OFA MIXTURE OF A A COMPOUND OF THE FORMULA
 2. A herbicide composition asclaimed in claim 1, wherein said weight ratio is 3:1 to 1:3.
 3. Aherbicide composition as claimed in claim 1, wherein compound b is1-phenyl-4-amino-5-chloropyridazone-(6).
 4. A herbicide composition asclaimed in claim 3, wherein said weight ratio is 3:1 to 1:3.
 5. Aprocess for suppressing growth of undesired or weed plants in cropplants which comprises applying to the host soil for said plants aherbicidally effective amount of a mixture of a a compound of theformula
 6. A process as claimed in claim 5, wherein said weight ratio is5:1 to 1:5.
 7. A process as claimed in claim 5, wherein compound b is1-phenyl-4-amino-5-chloropyridazone-(6).
 8. A process as claimed inclaim 7, wherein said weight ratio is 3:1 to 1:3.
 9. A herbicidecomposition comprising a herbicidally effective amount of a mixture of aa compound of the formula
 10. A process for suppressing growth ofundesired or weed plants in crop plants which comprises applying to theplants themselves a herbicidally effective amount of a mixture of a acompound of the formula
 11. A process as claimed in claim 10, whereinsaid weight ratio is 3:1 to 1:3.
 12. A process as claimed in claim 10,wherein compound b is 1-phenyl-4-amino-5-chloropyridazone-(6).
 13. Aprocess as claimed in claim 12, wherein said weight ratio is 3:1 to 1:3.